The Late Tony Bennett Was the First ‘Simpsons’ Guest Star to Play Themselves

Tony Bennett passed away today at the age of 96, and countless members of the music community now mourn the loss of the 20-time Grammy-winner. Though best remembered as an iconic American crooner, Simpsons fans can celebrate his legacy by throwing on a certain Season Two episode and watching him make history.

In the 1990 episode “Dancing Homer,” the burping, yelling, yellow patriarch lands a job as the mascot of a minor league baseball team, the Capital City Capitals, causing the Simpsons clan to relocate to the bustling metropolis during a montage sequence scored by a serenade from none other than Bennett himself. The family even meets Bennett, briefly, as they drive by the tuxedoed, bow-tied songbird, with Bennett remarking, “Hey, good to see you!”

While the moment is one of those blink-and-you-miss-it scenes that can slip by without note, in those five words, Bennett began a trend that would continue throughout the series as one of its staple narrative devices — in that scene, 33 years ago, Bennett was the first celebrity guest star in Simpsons history to appear as themselves on-screen. 

Bennett walked so that Buzz Aldrin could fly.